One of the most important things you’ll ever learn in a startup finance role? How to communicate upwards. Especially when that means supporting a first-time founder who’s juggling product, team, board, investors and now, you.

I say this to everyone in the FLF course: you don’t just manage numbers, you manage relationships. And the most critical relationship in your leadership toolkit is the one you have with the Founder or CEO.

It’s not the same as reporting to your old Financial Controller. You’re not waiting for instructions, you’re helping them run the company.

Let’s walk through what that actually means in practice.

1. Understand How a Founder Thinks

Founders are wired differently. They're usually fast, vision-first, decision-heavy, and allergic to detail. If you walk in with a 20-tab spreadsheet and no headline message, you’ve already lost them.

They’re not interested in whether creditors are up or down this month. They want to know what the numbers mean for runway, growth, and strategy.

Your job is to filter the noise and pull out the commercial story. What have you seen that helps them make better, faster decisions? Lead with that.

2. Stop Bringing Problems. Start Bringing Options

If you take one thing from this blog, make it this: your job is not to throw issues over the fence and hope the founder catches them.

They’re already drowning in decisions. So if you're flagging a problem, bring options.

• What are the possible ways to solve it?

• What are the risks or trade-offs?

• What’s your recommendation?

Don’t just say “X isn’t working.” Say, “Here are three ways we could fix X, and I recommend Option 2 because it balances short-term cost with long-term growth.”

That’s leadership. And it’s how you build real trust.

3. Listen Actively

You’re not just reporting upwards, you’re learning. When a founder gives feedback, don’t just nod and move on. Really listen. What are they actually worried about? What are they not saying?

You’ll often get clues about product direction, board pressure, or investor sentiment. The best finance leaders know how to tune into that frequency and use it to adjust course.

4. Regular Check-ins: Finding the Right Balance

Regular check-ins are essential, but don’t be the person who books a one-hour slot to walk through a monthly pack line by line. That’s not a check-in. That’s a hostage situation.

Find a rhythm that works; weekly 15-minute standups, sync updates via Slack, a monthly strategic session. And pay attention to how your founder likes to communicate. Some want a face-to-face. Others prefer bullet points over email. Many like a quick Slack message with a link to the dashboard.

You’ll probably figure this out by trial and error, but don’t be afraid to just ask: “What’s the easiest way for me to keep you in the loop without adding to your workload?”

They’ll appreciate it.

5. Be Honest. Even When It’s Uncomfortable

If there’s one non-negotiable in your relationship with the founder, it’s trust. That means being honest when something doesn’t look right. Forecast slipping? Flag it. Big VAT error? Own it, fast.

Don’t wait for month end. Don’t sugarcoat. Get the facts straight, propose a fix, and raise it early. Founders don’t expect perfection, they expect partnership.

And they definitely don’t want surprises in front of the board.

Being a strategic finance leader in a startup means more than reporting up, it means showing up. You’re there to help your founder steer the business through chaos, complexity, and growth.

It’s not about telling them what to do. It’s about helping them do it better, with clearer data, sharper insights, and stronger decisions.

So treat the founder relationship like the asset it is. Invest in it. Adapt to it. Lead it.

And if you’re not sure where to start, go book a 15-minute chat with your CEO this week. Ask them how you can make their life easier. It’ll open more doors than any spreadsheet ever will.

Want to be a confident and skilled Finance leader in 12 months?  Then follow these steps:

• Sign up to our next free workshop.

• Access the FLF Book that gives you an overview of the FLF Framework. 

• Work with me in the Financial Leadership Foundations course  for indepth training to become a confident & skilled finance professional in 12 months.  Includes regular Q&A sessions, networking with other finance professionals & the Advanced Management Accounts course.